3,5-dichloro-2-hydroxy-N-(p-tolyl)benzamide | 50728-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dichloro-2-hydroxy-N-(p-tolyl)benzamide
• 英文别名: 3,5-dichloro-2-hydroxy-N-(4-methylphenyl)benzamide
• CAS: 50728-73-9
• 化学式: C₁₄H₁₁Cl₂NO₂
• 分子量: 296.153
• InChiKey: BRMGEEGAOHIXQF-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±42.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-2-hydroxy-N-(p-tolyl)benzamide 、 氯甲酸乙酯 以 吡啶 为溶剂， 反应 1.0h， 以68%的产率得到6,8-Dichloro-3-(p-tolyl)-1,3-benzoxazine-2,4-dione
  参考文献：
  名称：

  抗分枝杆菌物质的化学结构与其对非典型菌株的活性之间的关系。第 14 部分：3-Aryl-6,8-dihalo-2H-1,3-benzoxazine-2,4 (3H) -diones

  摘要：

  6,8-二氯-3-苯基-2H-苯并恶嗪-2,4(3H)-二酮的八种衍生物和6,8-二溴-3-苯基-2H-1,3-苯并恶嗪-的九种衍生物苯环上取代的 2,4 (3H)-二酮是通过相应的水杨酰苯胺与氯甲酸乙酯反应制备的。在体外评估了这些化合物对结核分枝杆菌、堪萨斯分枝杆菌和鸟分枝杆菌的抗分枝杆菌活性。它们的活性随着苯环上取代基的疏水性和吸电子能力的增加而增加。

  DOI：

  10.1002/(sici)1521-4184(199801)331:1<3::aid-ardp3>3.0.co;2-2
• 作为产物：
  描述：

  3,5-二溴-2-羟基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,5-dichloro-2-hydroxy-N-(p-tolyl)benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of Closantel Analogues: Structural Promiscuity and Its Impact on Onchocerca volvulus

  摘要：

  Onchocerciasis, or river blindness, is a neglected tropical disease that affects more than 37 million people worldwide, primarily in Africa and Central and South America. We have disclosed evidence that the larval-stage-specific chitinase, OvCHT1, may be a potential biological target for affecting nematode development. On the basis of screening efforts, closantel, a known anthelmintic drug, was discovered as a potent and highly specific OvCHT1 inhibitor. Originally, closantel's anthelmintic mode of action was believed to rely solely on its role as a proton ionophore; thus, the impact of each of its biological activities on O. volvulus L3 molting was investigated. Structure activity relationship studies on an active closantel fragment are detailed, and remarkably, by use of a simple salicylanilide scaffold, compounds acting only as protonophores or chitinase inhibitors were identified. From these data, unexpected synergistic protonophore and chitinase inhibition activities have also been found to be critical for molting in O. volvulus L3 larvae.

  DOI：

  10.1021/jm200364n

文献信息

• Diamine-functionalized porous graphene oxide sheets decorated with palladium oxide nanoparticles for the oxidative amidation of aldehydes
  作者：Digvijay Sah、Surabhi、Padmini Gupta、Javaid Shabir、Manjeet Dhama、Subho Mozumdar

  DOI：10.1039/d2nj03807b

  日期：——

  In this work, a simple and stepwise strategy has been adopted for the successful synthesis of diamine functionalized porous graphene oxide sheets decorated with ultra-small palladium oxide nanoparticles. The successful synthesis, stepwise functionalization, morphology and elemental composition have been authenticated by using numerous physicochemical characterization techniques such as FT-IR, TGA,

  在这项工作中，采用简单而逐步的策略成功合成了装饰有超小氧化钯纳米粒子的二胺功能化多孔氧化石墨烯片。通过使用多种物理化学表征技术，如 FT-IR、TGA、粉末 XRD、SEM、HR-TEM、EDAX、元素映射、CHNS、ICP-MS 和 XPS 分析，对成功的合成、逐步功能化、形态和元素组成进行了验证. 制备的纳米催化剂已被用作可回收的催化剂，用于醛与胺的氧化酰胺化。这种纳米催化剂的主要特点包括反应条件温和、后处理程序简单、产品收率高、无任何有害副产物以及可循环使用多个催化循环。
• Discovery and Structure–Activity Relationships of Modified Salicylanilides as Cell Permeable Inhibitors of Poly(ADP-ribose) Glycohydrolase (PARG)
  作者：Jamin D. Steffen、Donna L. Coyle、Komath Damodaran、Paul Beroza、Myron K. Jacobson

  DOI：10.1021/jm200325s

  日期：2011.8.11

  The metabolism of poly(ADP-ribose) (PAR) in response to DNA strand breaks, which involves the concerted activities of poly(ADP-ribose) polymerases (PARPs) and poly(ADP-ribose) glycohydrolase (PARG), modulates cell recovery or cell death depending upon the level of DNA damage. While PARP inhibitors show high promise in clinical trials because of their low toxicity and selectivity for BRCA related cancers, evaluation of the therapeutic potential of PARG is limited by the lack of well-validated cell permeable inhibitors. In this study, target-related affinity profiling (TRAP), an alternative to high-throughput screening, was used to identify a number of druglike compounds from several chemical classes that demonstrated PARG inhibition in the low-micromolar range. A number of analogues of one of the most active chemotypes were synthesized to explore the structure activity relationship (SAR) for that series. This led to the discovery of a putative pharmacophore for PARG inhibition that contains a modified salicylanilide structure. Interestingly, these compounds also inhibit PARP-1, indicating strong homology in the active sites of PARG and PARP-1 and raising a new challenge for development of PARG specific inhibitors. The cellular activity of a lead inhibitor was demonstrated by the inhibition of both PARP and PARG activity in squamous cell carcinoma cells, although preferential inhibition of PARG relative to PARP was observed. The ability of inhibitors to modulate PAR metabolism via simultaneous effects on PARPs and PARG may represent a new approach for therapeutic development.
• US4724234A
  申请人：——

  公开号：US4724234A

  公开（公告）日：1988-02-09
• US4935450A
  申请人：——

  公开号：US4935450A

  公开（公告）日：1990-06-19
• Relationships Between the Chemical Structure of Antimycobacterial Substances and Their Activity Against Atypical Strains. Part 14: 3-Aryl-6,8-dihalogeno-2H-1,3-benzoxazine-2,4(3H)-diones
  作者：Karel Waisser、Jana Hladuvková、Jirí Gregor、Tomáš Rada、Lenka Kubicová、Vera Klimešová、Jarmila Kaustová

  DOI：10.1002/(sici)1521-4184(199801)331:1<3::aid-ardp3>3.0.co;2-2

  日期：1998.1

  6,8‐dibromo‐3‐phenyl‐2H‐1,3‐benzoxazine‐2,4(3H)‐dione, substituted on the phenyl ring, was prepared by the reaction of the corresponding salicylanilides with ethyl chloroformate. The compounds were evaluated in vitro for antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii, and Mycobacterium avium. Their activity increases with increasing hydrophobicity and electron‐withdrawing

  6,8-二氯-3-苯基-2H-苯并恶嗪-2,4(3H)-二酮的八种衍生物和6,8-二溴-3-苯基-2H-1,3-苯并恶嗪-的九种衍生物苯环上取代的 2,4 (3H)-二酮是通过相应的水杨酰苯胺与氯甲酸乙酯反应制备的。在体外评估了这些化合物对结核分枝杆菌、堪萨斯分枝杆菌和鸟分枝杆菌的抗分枝杆菌活性。它们的活性随着苯环上取代基的疏水性和吸电子能力的增加而增加。